It’s funny, after travelling around the United States on a road trip and other individual trips, I was a little worried that the things to do in Boston would seem quite ‘samey’ or ‘run-of-the-mill’ if you catch my drift? That’s not saying every place in the United States is the same. Far from!
But, there really are a few cities like New Orleans with all its incredible music, San Francisco with its culture and New York City for all its world-renowned spots that just seem to have such strong identities.
Thankfully, my fears and silly woes were totally blown out of the park once we arrived in Boston. I swear it’s one of my favourite cities in the United States.
And not just because of all the amazing (and pretty cheap) lobster you can get! We spent almost a week in the city and loved it. Take a look at some of the very best things to do in Boston during your first-ever visit to this East Coast city. You’ll love it!
1.) Stroll along The Freedom Trail
This is a Boston must-do! Every Bostonian that we spoke to said that the Freedom Trail was one of the best things to do in Boston.
This 2.5-mile road will take you past 16 historically significant sights (that are a total throwback), including the Boston Common, the Massachusetts State House, Granary Burying Ground, Park Street Church, and more.
You can either book this official Boston Freedom Trail walking tour or discover it at your own pace by following the red line that marks the route. Now, for us, we love this official tour as it’s by the very people who run and keep the legacy of the Freedom Trail alive. It’s so incredible and a great way to see the history of Boston.
The walking routes are easy to follow and a much more efficient way to see the trail if you’re looking to explore on your own terms and the full route. These walking tours are a great alternative if you want to get a deep insight into the significance of each place (and meet some fellow travel buddies on your trip).
The Freedom Trail Foundation has a really useful (and free) downloadable map that’ll also help you along your way. Oh, also, if you need a little pick-me-up, pop into the Thinking Cup, which serves some of the best coffee in Boston.
Fancy staying overnight in Boston? Make sure to book this room at the XV Beacon Hotel. Their Boston Common Suites are so nice, and the hotel feels like a proper little oasis in the heart of Downtown Boston. You will love it.
Read more: Best places to visit in Massachusetts
2.) Discover the Back Bay neighbourhood
Back Bay is one of my favourite little neighbourhoods and one of the best things to do in Boston during your visit. Whilst you’re in the area, make sure to check out the gorgeous and independent shops and stalls on Newbury Street.
There’s a whole heap of delicious cafes and restaurants too, just make sure to try out Saltie Girl Restaurant (Google Maps pin) for the tastiest seafood treats. We had the lobster and a tuna salad, and both were great. Just be aware, Saltie Girl can get very busy, so reserve a table in advance as it’s a busy little spot in Boston for lunch.
If you’re hankering for some East Coast seafood, pop into Luke’s Lobster Back Bay (Google Maps pin).
They make some of the best clam chowder and lobster rolls in the city. It’s a pretty casual joint and totally worth filling up at for lunch. Oh, also, they have the best blueberry soda I’ve ever tasted – You’ll love it!
Also, while you’re in the Back Bay area of Boston, you can also stop by the Boston Public Library to see its stunning Reading Room (Google Maps pin).
It’s totally beautiful and free to visit during opening hours. Just make sure to be respectful of those reading and studying whilst in the rooms.
Also, they have a lovely bar and restaurant where you can have afternoon tea in the Courtyard Tea Room within the famous library. It’s so beautiful but fills up fast, so reserve a table.
Afterwards, make sure to book this catamaran whale watching tour that’s just so incredible. Departing from One Long Wharf, the catamaran will take you out to spot humpbacks, finbacks, minke whales and dolphins. It’s one of the best things to do in Boston and perfect after scoffing your face with lobster rolls! Just be sure to book these tickets before arriving in Boston. Tickets can sell out at peak times.
Read more: Best places to visit in Massachusetts
3.) Ramble through Acorn Street
Acron Street (Google Maps pin) is one stunning little place to visit and is within easy reach of Boston Common. In my opinion, it’s one of the prettiest little cobblestone streets on the East Coast. It almost reminds me of some of the streets you see in Cambridge (England) or the villages of the Cotswolds (England).
There’s just something higgledy-piggledy about it, which makes it cute to see. Now, don’t expect to spend hours here. I think we only stayed about 20-30 minutes, but it’s well worth a gander at when you’re in the area. It really is very pretty.
If hunger calls, pop over to Tatte Bakery & Cafe (Google Maps pin), that’s relatively close by; they make an epic brew and have some delicious brunch rolls.
Alternatively, book this incredible day trip tour of Martha’s Vineyard. You’ll get picked up from your hotel and whisked off to experience the beauty of this very special island. Just make sure to book these Martha’s Vineyard tickets before arriving in Massachusetts; you don’t want to miss your opportunity to visit for a day trip.
Looking for the best hotel in Boston? Then make sure to book this room at The Langham. We stayed here during our last visit to Boston, and the hotel is stunning. Not only that, they have the prettiest cocktail bar (in the hotel), which is amazing for a nightcap. Oh, and be sure to go for lunch at the amazing Grana Restaurant. It’s situated right inside the historic hall of the Federal Reserve Bank’s grand hall. It’s absolutely iconic and totally beautiful. Plus, the food is exceptional.
Read more: Best places to visit in Massachusetts
4.) Visit Somerville for its foodie gems
Getting peckish? We love some restaurants and bars that we visited in the Somerville area of Boston (about 15 15-minute cab ride from Acorn Street. We loved visiting Field and Vine for their seasonal menu and also Celeste (Google Maps pin) for the tastiest Peruvian food and cocktails.
Also, for a great wine restaurant, head to Juliet. Such a great little place for lunch and nibbles. They have a great wine selection, and it’s so lovely.
If you’re staying for the evening, pop by Backbar, which is right next door to Field and Vine. This speakeasy-type bar is so kitsch and totally of the area.
We loved it, and everyone is so warm and friendly. Oh, and always make sure to take your ID with you.
5.) Watch a game at Fenway Park
Now, I’m not the biggest sports fan (unless it involves cake and tea, which it rarely does), but I have to say that I love experiencing a whole different sporting event when visiting a new place, with baseball being the game to experience in Boston.
Whether you’re a baseball fan or not, you’ve got to visit the home of the Boston Red Sox at Fenway Park. Even if you can’t catch a game during your visit, I’d recommend booking this one-hour guided walking tour of this iconic site, which is the oldest major league baseball park still in use. Oh yeah, and be sure to grab a picture of the 37-foot-tall left field wall popularly known as the Green Monster.
Also, another beautiful hotel in Boston is The Eliot Hotel. It’s in the Back Bay area of Boston and is perfect to explore some of the city’s independent cafes, cool restaurants and bars. Plus, the hotel itself is stunning, especially as it’s housed in one of the city’s historic townhouses.
6.) Ride the Swanboats at Boston Public Garden
For some quiet, head to the lush Boston Public Garden. Famous for being America’s first public botanical garden, you can see plenty of exotic trees, colourful flowers, and even take a ride on the swan boats (Google Maps pin) that are totally cute and kitsch.
Just remember, the swan boats are only open in the summer months. It’s a historical and fun experience, especially if you want a more chilled day.
If hunger beckons, grab brunch at the nearby (and charming) 75 Chestnut (Google Maps pin) when you’re in the area. They make the tastiest fall-harvest waffles.
Afterwards, head over (in a cab) to the Dovetail Restaurant in the Charleston area of Boston. It’s right within the historic Navy Yard and great to enjoy an alfresco dinner in the warmer months.
7.) Museum of Fine Arts
With over half a million works of art, including Impressionist paintings, early American art, Asian, and Egyptian collections, the MFA is going to satisfy any cravings you have for art.
Now, on the flip side, if you’re not really into ‘art’, then I’d probably recommend you steer clear of this spot.
Like I said, if you’re a total art fiend, you’ll find this spot to be one of the best things to do in Boston. Just make sure to check their website to see what their current and upcoming exhibitions are. It’s so amazing, and you can easily spend a lazy morning in Boston within the many rooms.
Fancy a tipple in a pretty unique speakeasy within an iconic hotel in Boston? Then get yourself over to the Encore Hotel, that’s just shy of Assembly Row in Boston. It’s around a 20-minute cab ride from MFA, but so worth it for the intimate venue of Old Wives’ Tale (Google Maps pin).
There’s only room for about 20 guests inside, so make sure to book on their website. The cocktails are great, and it’s easily one of our favourite speakeasies in Boston. Plus, it’s a great place to stay overnight if you want a more resort-like, full-service hotel that’s within easy reach of Downtown Boston.
8.) Gorge at Faneuil Hall and Quincy Market
In a lot of ways, Faneuil Hall reminds me of Borough Market in London (is that just me?). It’s filled with loads of little food carts and
Combine your love for history with your love for shopping at the Faneuil Hall Marketplace. Consisting of four buildings, the Faneuil Hall, North Market, South Market, and Quincy Market, this historic marketplace is full of unique shops, chain stores, street performers, and tons of food stalls and restaurants.
Even if you only end up window shopping, it’s a fun place to spend a couple of hours.
Read more: Best places to visit in Massachusetts
9.) Stroll through the Isabella Stewart Gardner Museum
Fashioned after the Palazzo Barbaro in Venice, the Isabella Stewart Gardner Museum houses the personal art collection of Isabella Stewart and is totally gorgeous.
You can see tons of American, Asian, and European art, including the works of Italian masters like Raphael and Titian. There are also old photographs, sculptures, furniture, and rare books. Plus, you can stroll in a skylit courtyard that is full of beautiful plants and flowers.
Visits take around 75 minutes, and it’s so worth visiting if you love art history. The whole museum is incredible and, for us, a total highlight to visit. Plus, it’s all indoors, making it a great spot to visit in Boston if the weather gets a little wet!
Also, if you have a Go Boston Card, you can enter for free on your birthday or if your name is Isabella… why was my name not Isabella! Alternatively, make sure to purchase advance tickets on their website – it can get very busy.
10.) Experience the Boston Symphony Orchestra
Classical music aficionado or not, you simply cannot miss attending a performance by the Boston Symphony Orchestra at Symphony Hall.
With more than 250 shows every year, you’re sure to catch something during your stay. Check their website for more information about upcoming performances and seasonal offers they have.
11.) Visit the Oldest Public Park, Boston Common
The Boston Common (Google Maps pin) is best known for being the oldest public park in the country. You may be lucky enough to catch a live theatre or musical performance while you’re here. If not, it’s still a wonderful park for a picnic or a lazy stroll.
The Common is one of the best things to do in Boston, during any season. For instance, if you’re visiting in winter, the Frog Pond has some pretty epic skating, too.
Though if you’re visiting in the Fall, you’ll get to experience the gorgeous colour change that makes the northeast coast so picturesque at this time of year.
Read more: Best places to visit in Massachusetts
12.) Explore the Paul Revere House
A true history lover’s gem, the Paul Revere House is one stunning piece of history and one of the best things to do in Boston, for sure.
Best of all, the house is on the Freedom Trail, meaning it’s an easy little stop to make on your trail across Boston (and still looks like it did way back in the late 1700s).
With period pieces, some fine silver, sweeping beams, original furnishings, and historic fireplaces, this is a great place to get a glimpse of American history that’s perched right in front of you.
13.) See the history at Granary Burying Ground
It sounds pretty macabre, and possibly not one of the best things to do in Boston for every visitor, but give this one a chance before you write it off.
The history of Boston is often defined by the people who ‘made it,’ and the Granary Burying Ground (Google Maps pin) is one of the oldest in the city (from the 1600s).
Take a wander through this peaceful little spot and learn more about the historic figures who once called Boston home. Many notable people are buried here. Best of all, it’s really easy to wander around as it’s part of the Freedom Trail, too.
You’ll probably only spend around 15-20 minutes here, but it’s a great place to learn more about the region’s history.
Read more: Best places to visit in Massachusetts
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